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Built by Sefton Henry Parry as the Royal Avenue Theatre, it opened on 11 March 1882 with 1200 seats. The first production at the theatre was Jacques Offenbach's Madame Favart. In its early seasons, the theatre hosted comic operas, burlesques and farces for several years. For much of this time, the low comedian Arthur Roberts, a popular star of the music halls, starred at the theatre. By the 1890s, the theatre was presenting drama, and in 1894 Annie Horniman, the tea heiress, anonymously sponsored the actress Florence Farr in a season of plays at the theatre. Farr's first production was unsuccessful, and so she prevailed upon her friend, George Bernard Shaw, to hurry and make his West End début at the theatre with Arms and the Man in 1894. It was successful enough to allow him to discontinue music criticism to focus full-time on play writing. The legendary actress Gladys Cooper managed the theatre for some years.

The theatre was rebuilt in 1905 to the designs of Blow and Billerey. During the work, part of the roof of the adjacent Charing Cross railway station collapsed. The roof and girders fell across the train lines but part of the station's western wall also fell and crashed through the roof and wall of the theatre. This resulted in the deaths of three people in the station, and three workmen on the theatre site and injuries to many more. The theatre was repaired and re-opened as The Playhouse on 28 January 1907 with a one-act play called The Drums of Oudh and a play called Toddles, by Tristan Bernard and Andre Godferneaux. Shaw wrote a sketch entitled The Interlude at the Playhouse for the occasion.

The new theatre had a smaller seating capacity of 679. W. Somerset Maugham's Home and Beauty premièred at the Playhouse on 30 August 1919, running for 235 performances, and Henry Daniell appeared here in February 1926 as the Prince of Karaslavia in Mr. Abdulla. Nigel Bruce appeared in February 1927 as Robert Crosbie in Somerset Maugham's The Letter, and again in May 1930 as Robert Brennan in Dishonoured Lady. Alec Guinness made his stage début here in Ward Dorane's play Libel! on 2 April 1934. Daniell returned in November that year as Paul Miller in Hurricane.

The theatre was restored to its 1907 design by impresario Robin Gonshaw, opening again in October 1987 with the musical Girlfriends. A commercial building, Aria House, was erected above the theatre.

In 1988, novelist and politician Jeffrey Archer bought the Playhouse for just over £1 million. The following year, the theatre was offered commercial sponsorship by a financial services' company, and for a while it was known as the MI Group Playhouse. In 1991, the Playhouse became home to the Peter Hall Company, and a number of critically and commercially successful plays were performed there, including Tennessee Williams' The Rose Tattoo (1991), starring Julie Walters and Moliere's Tartuffe (1991), starring Paul Eddington and Felicity Kendal. Around this time the basement bar area of the theatre was converted into a private restaurant, Shaws, but the enterprise was unsuccessful and the space was later converted back into a bar/cafe.